Steve and I had been chatting for a couple of months. He reminded me of the man many years ago who introduced me to sexting or, as it was called in those days before smartphones, cybersex. It was in the old chat rooms that aren’t around any more. Back in then I was also a lot more innocent and was looking for romance more than anything. I found it and was deeply in the process of falling in love with Jack when he ghosted me, never to be seen again and breaking my married, young mother’s heart. It took months but after I recovered from the mental anguish , I resolved to never fall for anyone on line again but to just keep it all fun and sexy games.
That was when I was 27 but then at 40, Steve came into my life through Reddit. The internet and chat rooms had turned me from a young romantic into a woman with a secret life of kinky and perverted online sex. But I remained true to my marriage vows, at least physically. And I didn’t play online all the time. I went in phases where I would binge and then vow to never do it again but a few weeks or months later, there I was, back with a new username and kinkier than ever.
I had two huge fantasies that I could never get past. One of them I have had since my teens. The other is quite recent and came about as a result of hearing other women’s stories. It has become a source of both shame and incredible arousal. Steve shared that second fantasy and felt the same sense of shame. He was five years older than me, an idea age. I didn’t want to chat with grandpas and I found younger men to be too obsessed with what they have seen in porn, too misogynistic and too unresponsive to women’s needs over their own.
We clicked right away. I don’t remember if I answered his prompt in r/dirtypenpals or he replied to mine but the first time we met, we chatted for hours and I hadn’t been that turned on or orgasmed so hard from an online chat for a very long time. We chatted frequently after that diving deeper and deeper into our shared fantasies, our kinks and I have to confess, our perversions.
I began to think about him all the time. I saw the signs of repeating what had happened years ago. I made the decision that I wasn’t going to get ghosted again. So I ghosted him. I just stopped logging on and I was a very chaste, very dutiful wife and mother. The only time I logged on during that time was out of guilt to send him a message explaining why I wasn’t there any more.
I lasted two months two months and then I couldn’t stay away any longer. I logged back on, started looking at Dirtypenpal posts, found a couple of former chat partners and fell off the wagon hard. I didn’t contact Steve though. I wanted him to come and find me. I left traces of myself all over the NSFW subreddits hoping that he would see them but he never did. Every day I looked for a red envelope or chat notification from him but it never came. Finally. I couldn’t wait any longer. I had to swallow my pride and my desire to be hunted and wanted. Like a besotted teen, I sent him a message telling him I was back expecting a response within minutes like usually happened. After almost a week I decided that if he was still around he was no longer interested in me or even that his girlfriend may have discovered his online activities.
But then, one morning, when I logged on and checked my chats, there he was. He said after I ghosted him Reddit didn’t have the same appeal. What a gloriously dirty, orgasmic morning that was!
Up until this point, everything I have written is true to the best of my memory. Now it’s time to start the fiction and fantasy
After several hot chats, fantasies role played and little challenges given to one another, all combined of course with lovely orgasms, we settled into a pattern. We didn’t chat every time we were online and sometimes we didn’t even chat dirty. We became friends with benefits. He was my online male best friend and my very guilty secret. We reached the point where things would happen in our real lives and we couldn’t wait to see each other to tell about them. It was such a comfortable sexy friendship.
Then something happened that upset the whole equilibrium. Steve had to come to Arizona for a whole week for a work conference. It was worlds colliding in the best and the worst of ways. He was going to be so close. He didn’t make it any easier. We had chatted about how much trouble we could get into if we ever met and I, thinking it could never happen, played along with it. I think I must have encouraged him because he kept pressuring me. I had never even kissed another man on the lips since before I had been married and now I was contemplating meeting one to play out my dirtiest fantasies. I was in mental agony.
But, it is obvious what happened, otherwise this story would not have had any reason to have been written. About two weeks before his arrival I told him I would meet him at his hotel after the second day of his conference. I remember my hands shaking as I wrote the words and feeling so excited yet so guilty.
The day before our day of destiny he sent me a message. This is it.
“Before you come to my hotel room, you are to make the following preparations:
Eliminate all hair below your neck
Wear plain white cotton bikini panties
Wear a bra that flattens your breasts (they are pretty tiny, so that was’t too difficult)
Putting your hair into pigtails or braids is your choice
Wear a short, pretty little sundress and cute flat sandals
Be in character as in our last sexting session.
If you haven’t already guessed it, our favorite roleplay was me as a much too young girl and him as an older man. But there was a wrinkle that had come up in our last chat that was going to complicate things.
I spent the afternoon getting myself ready and told my husband and kids I was going to go shopping and may meet up with girlfriends later for drinks. I also told them that unless the house was on fire or somebody had to be transported in an ambulance to not call me because I needed a night off from being wife and mom. That part, at least was true.
I dressed in regular clothes and drove to Steve’s hotel, one of the luxury chains, and went into the ladies room by their big ballroom to change. I did my hair the way he wanted, put on the little dress which was way too short by my normal standards, did my makeup to look as young as possible. I am petite and blessed with good genes and in dim light can still pass for being in my twenties but Steve was going to have to use a lot of imagination to pretend I was his little tween slut.
When I was all done. I looked in the mirror. “God, I look like I’m working for a fantasy escort service,” I thought to myself. Briefly, I thought about going home or at least just putting on regular clothes but I remembered how aroused we had both been with the fantasy, slipped out of the rest room and hit the elevator button hoping it would be empty. Of course it wasn’t. Two middle-aged businessmen in suits tried, quite unsuccessfully, not to stare at me as we rode up to the fourteenth floor. I think I blushed several shades of red.
I left the elevator knowing those men were now talking about me, walked down the corridor to Steve’s room and when I arrived saw he had flipped the lock so it wasn’t all the way closed. I stood outside a second trying to decide if I should knock when, from inside the room I heard his voice for the first time.
“Come in Angie. Close the door behind you.”
I stepped through the door and closed it. I was so nervous. We had not even seen each other’s pictures before. Okay, I had sent him a pic of a woman who looked like me and he had, with my permission I may add, he is after all a gentleman, a couple of pics of his very nice, hard penis. Dick pics to be a little more accurate.
I was not disappointed. He was very handsome in that confident man in his 40’s way and thank god he didn’t have a big old belly. He looked at me and told me I was smoking hot. I think he meant it. It took me years to accept it but I am pretty, especially for my age but I told him I felt ridiculous dressed like this. He, on the other hand looked very relaxed in his suit trousers and his white long sleeved shirt open at the neck. His tie was lying on the bed.
“You’re not ridiculous,” He told me. “You are a character and until we decide to be ourselves, you are not to break it. Do you understand?”
I was impressed with his take-charge attitude. I’m a skinny petite little woman but I’m no pushover. Some would say I’m a feisty woman. My kids will tell you I’m a controlling bitch. But at that moment I was very happy to submit to Steve’s instructions.
He gave me a hug and a little peck on the lips.
“You remember our last chat, Don’t you?” I nodded.
“How were you acting,” he asked.
I looked down at my feet sheepishly. “I was being an entitled little brat,” I confessed.
“And how were you doing that”?
“I wouldn’t do my homework. I wanted to play our naughty games.”
“And what did I tell you that you needed?”
“You said I was being a spoiled little slut and needed a very hard spanking.”
I have to pause here to tell you that one of the sexual experiences I have craved for years is to be spanked really hard. My husband will try but he is a very gentle man. The thought of him causing me pain is just too much. He would rather give me a long massage with a very happy ending. I shouldn’t complain but here I am. Just an entitled little brat.
Steve took me by the elbow and led me across the room and stood me facing the work station. He took the hem of my dress in his hands and lifted it over my head. I wasn’t wearing a bra because the top was rouched and elastic. It gave my little breasts all the support that was needed. I stood in front of him in just my panties. Then he ordered me to bend over it, grasp the far edge with my hands and then step back until my arms were outstretched. My head lay on the edge of the desk but the rest of my body was off of it. He put one hand on the small of my back and pressed down making me arch it.
“Stay just like this. Don’t move.”
I obeyed.
“Such sexy little girl panties, aren’t they? Do you feel very naughty wearing them?”
I nodded. I didn’t tell him I had taken them from my daughter’s underwear drawer.
He hooked his fingers into the elastic waistband and pulled them all the way down, pausing to take off my slip on sandals before having me step out of them. He made me stand with my legs quite wide apart. My pert little bottom was on full display as was my rapidly dampening pussy. I felt so exposed. And so turned on. I wiggled my butt at him teasingly.
“Do you like my bottom, Uncle Steve? I can’t wait for you to touch it. I’m a very dirty girl, aren’t I?”
I felt so exposed. And so turned on. My clitoris was tingling and I could feel myself getting wet.
“Oh you would like that wouldn’t you? You would like me to play dirty games and distract me from your punishment. Just like you wanted to play them to avoid doing your homework. Let me tell you, young lady, I am the adult here and you need to be punished. Now, stop moving towards the desk. Move backwards.”
I took a couple of small steps backwards until my arms were stretched out again. The air conditioner kicked on and I felt the cold air blowing on my little butthole and the coolness of it on my wet pussy. Steve stood to one side of me. He unbuckled his belt and pulled it from the loops. I bit my lower lip in anticipation.
“Don’t forget the safe words. Remember Yellow is slowdown or back off. Red is Stop. Don’t be ashamed to have to use either of them. Are you ready?”
By now my mind was going in a hundred different directions. I was more than scared. It took all I had to not tell him to just give me a light spanking but I had been craving this for so many years. I may never get another opportunity to experience it. My mouth was dry and I was trembling.
“Yes. I’m rea…”
Before the words had even left my mouth the first stroke came down. Oh my God! How it hurt! The sting was instant and then it spread across my cheek like fire. Instinctively I let go of the desk top and jerked upright. My hand went behind me to rub the pain.
Steve grasped both my wrists and forced me back down. As he did, his crotch pressed against my hp and I felt his erection. I bit my lip again and whimpered in pain. He stepped back ordering me to stay in place or the punishment would be worse.
The belt came down again on the other cheek. I didn’t let go of the desk but my foot kicked back and my body did a spiral movement. It was so much worse when I couldn’t jerk upright. This time he waited until I stopped breathing quite so hard and was able to stay still as the pain slowly dissipated. As it did, I realized my level of arousal increased. so much was going through my mind. I remember thinking to myself that this was the experience I had dreamed of and fantasized about for so many years. I was getting to live the porn videos I had watched so many times and masturbated to. I had some favorites that I had watched over and over and realized that my body was acting just like the girls in those most realistic ones that turned me on the most. I determined in my mind that I was going to live this out have the fullest experience possible from this very special time.
“Steve,” I whimpered. “Can I touch myself Can I touch my pussy. Please?”?
It was obvious that he had planned this encounter to the smallest detail but I think that my question actually surprised him.
“Touch yourself? Oh you dirty little slut. There is your entitlement again. This is a punishment for being a bad little girl. Don’t you dare take your hands off of that desk.”
I remained in place. Bent over with my arms outstretched. My back arched raising my ass and my pussy higher putting me on maximum display. Steve reached between my legs and cupped my perfectly shaved, perfectly smooth pussy and one finger probed between my swollen lips.
“God, you’re so wet!”
I think he broke character briefly and was genuinely surprised. He slid his finger along my wet slit and rubbed the wetness on my clit. My hips rocked in involuntary reaction. After a few seconds, to my great disappointment, he took it away .
“Don’t think your wet little cunt is going to distract me from spanking you. I’m not that easily manipulated.
The belt came down with fierce severity on my little ass once again. This time on the same cheek as the first stroke but higher up. I gasped, moaned and writhed. Then he did the same thing on the other cheek. Another one on the first side but lower down and then on the other. He paused for a few seconds between each stroke allowing me to react, my body to writhe in the short-lived agony and to reset my position.
The pain and the arousal increased in intensity. My eyes were tearing up and I didn’t know if I was going to scream in agony or moan in arousal. I could hear him breathing heavily too. I bet he was as turned on as me. I thought about his hard cock that I still had not seen other than in the pics he sent me. I hoped it was so hard it hurt him trapped in his suit pants.
His hand reached between my legs again, not exploring this time but deliberately touching me to arouse me even more. His fingers pushed deep inside my vagina and he curled them downwards to rub my g-spot. Damn! This man knew his way around a pussy. He pulled them out but only to use them on my clit, rubbing and massaging it until I groaned in pleasure once again. And then, once more, he stopped and whipped my poor painful ass with that thick leather belt.
The same pattern only six strokes this time. Alternating between my cheeks and never in the same place twice. My whole little ass was on fire. I writhed with each stroke. When the belt landed at where my thigh met my bottom, just millimetres from my pussy, I screamed.
“Angie, keep quiet. We don’t want anyone calling the police, do we?”
He put his hand over my mouth and hit me the same way on my other cheek. I screamed into his hand as my body tensed up yet again.
Then he was fingering me and rubbing my clit again. He was in no hurry. Pushing his long, thick fingers inside me, stretching the walls of my vagina. Massaging my clit, gently then roughly, then gently again. Rubbing his fingertip, wet with my creamy juices on my little rear hole and pushing gently. I was writhing again, not only in pain now but in pleasure also. He brought be to the very edge of cumming before backing off leaving me panting as I still obediently held on to the far edge of the desk. Then he started again. It took no time to have me right there on the edge again.
I lifted my head from the desk surface to speak “Make me cum. God, Steve. Please let me cum.”
His response was to his hands away completely. Tears were running down my cheeks from the pain of the spanking. My pussy was on fire. My clit was so swollen it was throbbing. I needed to cum so badly at this point. I couldn’t stop myself. I let go of the desk with one hand and thrust it between my legs, furiously rubbing myself.
The hand holding the belt grasped my wrist and set it back in place. At the same time, he slapped my face hard. I froze, stunned and began crying.
“I told you to stay in place. Now you get spanked more.”
That belt came down on my bottom over and over again. He methodically whipped the same spots as before. This time, because I was so tender it hurt even more but he showed mo mercy. There was no pausing between strokes now. It was one after the other. I swung my hips from side to side. I kicked my feet up. I swayed forward with each blow.
It was such exquisite agony.
And then it was over.
He lay his belt on the desk and put his hand on my bottom and began to rub. I was whimpering, crying, tears running down my face. When I got to see myself in the mirror, my makeup was a mess. But when his fingers began their exploration again my body responded enthusiastically. I pushed back against his probing fingers feeling them deep inside my soaking wet pussy. I moaned in pleasure as he rubbed my clit. He pushed me forward so now my torso was lying on the desktop
He stepped away. “Don’t move, he ordered and I looked back and he was pulling his clothes off. His crisp white shirt lay on the floor. He unbuttoned his pant and he let them fall to the floor before kicking them off and he stood to my side in his grey boxer briefs, his hard cock making a big tent in the front and then he pulled them down and I got to see it in the flesh for the very first time in al its rampant glory.
This is where he went off script. In our dirty Reddit chats he never put his cock inside me because my immature little pussy would have been much too tight still. He had taught me to use both my little hands to stroke him to orgasm. I had sucked on it until he came in my mouth. He had jerked off and shot his cum all over my bald little cunt and, my favorite I had straddled him as he lay on his back with his cock pressed between my lips ans slid up and down, back and forth until we both came, leaving a sticky mess on our tummies.
But the game was we never fucked. And now he broke the rules. He stepped behind me and pressed against me. He was so tall his balls actually rested on top of my ass. Then he must have almost kneeled because I felt the head of his cock being rubbed along my pussy getting coated with my lubrication. Then he pushed it inside me. For a second, I panicked. This wasn’t supposed to happen. I had never cheated before and, as absurd as it sounds given what had gone down in the last half hour, I had told myself that anything less than penetrative sex still wouldn’t really count. I would just have been getting something out of my system. Such is how we rationalize our behavior.
He pushed deep inside me. He must have straightened his knees because my feet actually came off of the floor lifted by his big cock. He pushed me forward so I was lying across the desk with my feet dangling down. I wrapped my legs around his and he pumped in and out of me. My clit was pressed down against the hard top and with each thrust I rocked backwards and forwards, massaging it.
I was out of character now. I was no longer a little girl. I was a 40 year old woman getting fucked hard by a man who wasn’t my husband. I felt so slutty, something that in my religious youth I never got to be. I liked the feeling and I liked it even more when he grabbed both of my braids and pulled my head back.
It was all to much. My orgasm was building fast and I wasn’t going to delay it. I felt the familiar tightening of my insides and knew I had reached the point of no return. My clit ground down hard on the desktop .
“You little fucking slut. Cum on my cock”
That is all it took. My body stiffened and I felt the first wave of orgasm sweep through my cunt. I may be little but I’m not quiet. I began screaming and Steve clamped his hand over my mouth and pushed a finger inside. My orgasm was huge and it was one of the longest ever. At one point I felt him cum inside me and that sent another wave through me.
Finally I was done. Steve released me and we both stood up. I felt so awkward until he took me in his arms and held me.
*The ending seemed a little abrupt but then my online BFF told me she thought about him sending me home with his cum leaking out into my daughter’s panties. I think I will leave it with that thought.*
Source: reddit.com/r/sexystories/comments/h12bfa/i_met_my_online_lover_in_a_hotel_room_f40_mf_mf